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Phosphonium Salts as Pseudohalides: Regioselective Nickel‐Catalyzed Cross‐Coupling of Complex Pyridines and Diazines
Author(s) -
Zhang Xuan,
McNally Andrew
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201704948
Subject(s) - phosphonium , nickel , chemistry , catalysis , aryl , combinatorial chemistry , halide , palladium , reactivity (psychology) , regioselectivity , coupling reaction , substrate (aquarium) , pharmacophore , phosphonium salt , organic chemistry , stereochemistry , alkyl , medicine , alternative medicine , oceanography , pathology , geology
Heterobiaryls are important pharmacophores that are challenging to prepare by traditional cross‐coupling methods. An alternative approach is presented where pyridines and diazines are converted into heteroaryl phosphonium salts and coupled with aryl boronic acids. Nickel catalysts are unique for selective heteroaryl transfer, and the reaction has a broad substrate scope that includes complex pharmaceuticals. Phosphonium ions also display orthogonal reactivity in cross‐couplings compared to halides, enabling chemoselective palladium‐ and nickel‐catalyzed coupling sequences.